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Dear Jewish Singles,

I wanted to share with you some of my personal dating experiences, and how those may inform your dating life during this challenging and unpredictable period of COVID-19 pandemic.


There I was, I was finally ready to date. I thought I did everything right, the stage was set, I was where I wanted to be, and indeed I started dating. And then, the 2008 recession hit. Predictability was no longer a strong factor; economic anxiety was in the air. Many who had planned their careers in the field of finance were not going to get a paying job in the field. Those who had gotten into prestigious law schools taking out large loans knew they may not be able to pay those. People who thought their parents would be able to support them in their early years of marriage realized that won’t happen. Many of those who had jobs suddenly didn’t.

This had a significant impact on my dating life, and many of my friends’ dating lives.

Dating styles had suddenly changed. Those who expected to afford to take a girl out with a certain kind of car to certain kinds of restaurants would no longer be able to do it. Those who planned on traveling more for dates were no longer able to afford it. Those who thought they would be able to project financial confidence would no longer be able to do that. Everything had changed. We had hit a recession like the world had not seen since 1929. No one knew what to expect. Kind of like what we are seeing now in the world, minus the pandemic.

Different people had different reactions.

Some decided to push off dating altogether, others chose to limit their dating in one way or the other. In contrast, others felt they were changing the course of their lives and thus needed to change the type of person they would be dating. Some would just need more time to figure out their next steps.

Having that hindsight, I would urge those who are dating during this most unpredictable in recent history: do not put your foot on this break. Do not alter your plans to build a home together with someone you love, do not shy away from pursuing a relationship you believe in. It may get difficult, but reflecting on history, I believe you are far better off hitting the pedal, than hitting the break.

My friends who took the risk in those early days of the recession, I believe, fared better for themselves in an unstable world and are far better off than those who proceeded with caution. Yes, it may have meant they had to relocate to a more affordable state. It may have meant they had to find a career in a field they had not expected. Or it may have meant that everything worked out as planned. Avoiding risk altogether as a strategy was not a winning approach.

Mark Twain famously said: “In this world, nothing is certain except death and taxes.” There are few things that guarantee us what the future will be like. Finding someone who will be at your side during those times of uncertainty and change can make all the difference. Lowering expectations and embracing for a less predictable ride can lead you into the best thing that has ever happened to you. To quote Billy Joel’s Piano Man: “Yes, they’re sharing a drink they call loneliness. But it’s better than drinkin’ alone”.

As matchmakers, my wife and I feel the pain of those having to date during these times of turmoil, yet are encouraged by seeing people widening their dating pool during these tumultuous times. People who in the past would not say yes to dating that person or the other, are saying yes. People who would not agree to date often are doing so now. We salute you all. Perhaps, now more than ever is a time to find someone to be at your side as we journey towards a world that will never be the same.

Dating at a time you can’t even meet someone in person is most definitely something that has not been tried before. And yet, I would urge you, now more than ever, to find a way to take this journey with someone at your side. If our own grandparents had expected a predictable world, we would never be here.

Who in Jewish history knew for how much longer they will be living in the same country or under the same circumstances or with what kind of livelihood? Jews have shown the world how embracing uncertainty together can lead to the most spectacular results. This generation should be no exception.

As so many of the people we know, care for, love hosting for Shabbat meals– or have never met– are facing the added stress of how to date during these difficult times, my wife and I are here to let you know: we are cheering you on. We are rooting for you. Dating is never easy, how so much more so during these unusual times. We believe in you, care for you, and applaud your faith in a better tomorrow—together. Good luck!


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Rabbi Elchanan Poupko is a rabbi, writer, teacher, and blogger ( He lives with his wife in New York City.